NP-MRD: Showing NP-Card for (1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate (NP0223720)

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Record Information

Version

2.0

Created at

2022-09-06 01:53:48 UTC

Updated at

2022-09-06 01:53:48 UTC

NP-MRD ID

NP0223720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate

Description

JATAMANVALTRATE M belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate is found in Valeriana jatamansi. Based on a literature review very few articles have been published on JATAMANVALTRATE M.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062203532D          

 27 29  0  0  1  0            999 V2000
    1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5152    5.7705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    5.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5235    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360    3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235    3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7610    3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    3.8701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0420    3.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267    3.3180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 16 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 27  1  6  0  0  0
M  END


  Mrv1652309062203532D          

 27 29  0  0  1  0            999 V2000
    1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5152    5.7705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    5.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5235    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360    3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235    3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7610    3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    3.8701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0420    3.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267    3.3180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 16 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0223720

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOCC1=CO[C@@H](OC(=O)CC(C)C)[C@@H]2[C@@]3(CO3)[C@H](C[C@@]12O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O8/c1-5-23-8-13-9-24-17(27-15(21)6-11(2)3)16-18(13,22)7-14(26-12(4)20)19(16)10-25-19/h9,11,14,16-17,22H,5-8,10H2,1-4H3/t14-,16-,17-,18+,19+/m0/s1

> <INCHI_KEY>
HXMXOBXOPPGJHP-GPFWEFOESA-N

> <FORMULA>
C19H28O8

> <MOLECULAR_WEIGHT>
384.425

> <EXACT_MASS>
384.178417862

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.8171234887882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-4a,5,6,7a-tetrahydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-1-yl 3-methylbutanoate

> <JCHEM_LOGP>
-0.1081836013333341

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.493815956632005

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4576049005691596

> <JCHEM_POLAR_SURFACE_AREA>
103.82000000000002

> <JCHEM_REFRACTIVITY>
92.46019999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxirane]-1-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.000  12.320   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.000   3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.828  10.772   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.132   9.716   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.037   8.470   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.577   8.470   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.347   7.136   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.577   5.803   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -8.887   7.136   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.132   7.224   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.812   5.718   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.276   6.194   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    8   17   25                                                  
CONECT   17   16    5   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   16   26   27                                             
CONECT   26   25   27                                                       
CONECT   27   26   25                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
JATAMANVALTRic acid m	Generator

Chemical Formula

C₁₉H₂₈O₈

Average Mass

384.4250 Da

Monoisotopic Mass

384.17842 Da

IUPAC Name

(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-4a,5,6,7a-tetrahydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-1-yl 3-methylbutanoate

Traditional Name

(1S,4aS,6S,7R,7aS)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxirane]-1-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CCOCC1=CO[C@@H](OC(=O)CC(C)C)[C@@H]2[C@@]3(CO3)[C@H](C[C@@]12O)OC(C)=O

InChI Identifier

InChI=1S/C19H28O8/c1-5-23-8-13-9-24-17(27-15(21)6-11(2)3)16-18(13,22)7-14(26-12(4)20)19(16)10-25-19/h9,11,14,16-17,22H,5-8,10H2,1-4H3/t14-,16-,17-,18+,19+/m0/s1

InChI Key

HXMXOBXOPPGJHP-GPFWEFOESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Valeriana jatamansi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Iridoid-skeleton
Bicyclic monoterpenoid
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.11	ChemAxon
pKa (Strongest Acidic)	13.49	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.82 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	92.46 m³·mol⁻¹	ChemAxon
Polarizability	39.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00047476

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101472681

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate (NP0223720)

MOL for NP0223720 ((1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

3D MOL for NP0223720 ((1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

3D SDF for NP0223720 ((1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

3D-SDF for NP0223720 ((1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

PDB for NP0223720 ((1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

3D PDB for NP0223720 ((1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

SMILES for NP0223720 ((1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

INCHI for NP0223720 ((1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

Structure for NP0223720 ((1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

3D Structure for NP0223720 ((1s,4as,6s,7r,7as)-6-(acetyloxy)-4-(ethoxymethyl)-4a-hydroxy-1,5,6,7a-tetrahydrospiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)